2,3-二氢苯并呋喃-5-甲醛合成路线 （共 30 条）
反应条件
1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 1.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 3.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 4.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 5.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 6.1: SOCl2 / 75 °C 7.1: AlCl3 / 1,2-dichloro-ethane / 20 °C 8.1: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C 9.1: NaH / tetrahydrofuran / 20 °C 9.2: 60 percent / tetrahydrofuran / 20 °C 10.1: 81 percent / H2; ethanolic NH3 / Raney-nickel / 40 °C / 3600.36 Torr View Scheme
参考文献
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239
反应条件
piperidine in pyridine 4 h; Reflux;
参考文献
Chen, Wen; Yang, Li-Juan; Li, Yan; Wang, Xue-Quan; Wang, Shao-Jie; Wan, Wei-Chao; Zhang, Hong-Bin; Yang, Xiao-Dong
Letters in Drug Design and Discovery, 2013 , vol. 10, # 7 p. 561 - 571
反应条件
potassium hydroxide; iodine T=0°C; 4 h;
参考文献
Saitoh, Morihisa; Kunitomo, Jun; Kimura, Eiji; Hayase, Yoji; Kobayashi, Hiromi; Uchiyama, Noriko; Kawamoto, Tomohiro; Tanaka, Toshimasa; Mol, Clifford D.; Dougan, Douglas R.; Textor, Garret S.; Snell, Gyorgy P.; Itoh, Fumio
Bioorganic and Medicinal Chemistry, 2009 , vol. 17, # 5 p. 2017 - 2029
反应条件
sodium tetrahydroborate in methanol T=20°C; 15 h;
参考文献
Takeda Chemical Industries, Ltd.
Patent: EP1199304 A1, 2002 ;
Location in patent: Referential example 79 ;
EP 1199304 A1
反应条件
N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in chlorobenzene T=80°C; 1 h;
参考文献
Saitoh, Morihisa; Kunitomo, Jun; Kimura, Eiji; Iwashita, Hiroki; Uno, Yumiko; Onishi, Tomohiro; Uchiyama, Noriko; Kawamoto, Tomohiro; Tanaka, Toshimasa; Mol, Clifford D.; Dougan, Douglas R.; Textor, Garret P.; Snell, Gyorgy P.; Takizawa, Masayuki; Itoh, Fumio; Kori, Masakuni
Journal of Medicinal Chemistry, 2009 , vol. 52, # 20 p. 6270 - 6286
反应条件
1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 1.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 3.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 4.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 5.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C View Scheme
参考文献
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239
反应条件
1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 1.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 3.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 4.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 5.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 6.1: SOCl2 / 75 °C 7.1: AlCl3 / 1,2-dichloro-ethane / 20 °C View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 45, # 19 p. 4222 - 4239
反应条件
1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 1.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 3.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 4.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 5.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 6.1: SOCl2 / 75 °C 7.1: AlCl3 / 1,2-dichloro-ethane / 20 °C 8.1: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C View Scheme
参考文献
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239
反应条件
1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 1.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C View Scheme
参考文献
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239
反应条件
1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 1.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 3.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 4.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C View Scheme
参考文献
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239
